Potassium Iodide → cis-4-(benzoylamino)-3-methoxy-N,N-dimethyl-alpha,alpha-diphenyl-1-piperidinebutanamide

HRID 1088395ノート

反応式

HRID 1088395 の反応式
[Br-].[C:2]1([C:8]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11][O:10][C:9]2=[N+:13]([CH3:15])[CH3:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][O:23][C@H:24]1[C@@H:29]([NH:30][C:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:28][CH2:27][NH:26][CH2:25]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[C:31]([NH:30][C@H:29]1[CH2:28][CH2:27][N:26]([CH2:11][CH2:12][C:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([N:13]([CH3:15])[CH3:14])=[O:10])[CH2:25][C@H:24]1[O:23][CH3:22])(=[O:38])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 2723589(Dihydro-3,3-diphenyl-3H-furan-2-ylidene)dimethylammonium bromideHCID 15096867cis-N-(3-methoxy-4-piperidinyl)benzamide

生成物 1

HCID 15096783cis-4-(benzoylamino)-3-methoxy-N,N-dimethyl-alpha,alpha-diphenyl-1-piperidinebutanamide収率 35%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 7909Methyl Isobutyl Ketone溶媒

実験手順

A mixture of 7.6 parts of N-(dihydro-3,3-diphenyl-2(3H)-furanylidene)-N-methylmethanaminium bromide, 4.7 parts of cis-N-(3-methoxy-4-piperidinyl)benzamide, 3.8 parts of sodium carbonate, 0.1 parts of potassium iodide and 240 parts of 4-methyl-2-pentanone was stirred and refluxed for 18 hours using a water-separator. The reaction mixture was cooled to room temperature and washed with water. The organic phase was separated, dried, filtered and evaporated. The oily residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 3.5 parts (35%) of cis-4-(benzoylamino)-3-methoxy-N,N-dimethyl-α,α-diphenyl-1-piperidinebutanamide; mp. 146.6° C. (compound 122).

後処理

  1. temperaturerefluxed for 18 hours
  2. washwashed with water
  3. customThe organic phase was separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily residue was purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from 2,2'-oxybispropane
  12. filtrationThe product was filtered off
  13. customdried

出典と根拠

ORDレコード
ord-d4b8e95b03814591bd2a9b016f1324e0
出典データセット
uspto-grants-1990_10
特許番号
US04962115

反応ノート

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